@Danielle Zito We did this (reappraised a three-decker in Boston to apply for a HELOC to fund investment down payment on another, also Boston) and though rates are variable on the product we have, they're fixed for a period of time first - so paying it back is a priority.In terms of timing, it does take some time to get through the HELOC process, so you probably want to start sooner rather than later, but I would discuss with your mortgage lender as well.

He agreed to join in investing with me and work for me for no costs at the start of our business (all income would be going back into the business until it's financially self-sufficient)On top of that HUGE benefit seeing as contractors absolutely drain cash during a rehab, my dad told me that he will possibly help financially support me in the start of my business.

Low-cost index funds in your desired asset allocation.  4% withdrawal rate.  

I’ve been going back and forth between whether I want to wait until I have the funds to purchase a property for this purpose vs obtaining a lease and subletting that property when I am not in town (with landlord permission of course).

If you don't have the reserve funds going into a investment property you are not in a position to invest. 

Colonial Funding might do them that small as well as a small / medium investor.

This one is easier as there's natural gas lines and I can just convert it over but still pricey ($5-7k)The seller doesn't have the funds to make the repairs so I'm trying to find a way to make this deal happenWithout getting bids, I'm estimating about $15-20k for rehabbing these items (FEEL FREE TO TELL ME I'M WAY OUT TO LUNCH)....this is on top of the $5-8k I budgeted to put into the interior.I'm not a flipper and was looking at this as a buy and hold cash flowing property.Looking where to go with this one:A) Reduce offer by $15-20k to $155k- Cons: I'm going to have to find a loan as I need my capital for other purchases in the hopperB) Reduce to $160k and get $5k in closing help- Cons: I'm still going to be out of pocket but b/n closing help and reduced downpayment would be able to get most of the work done and just put the rest on a credit card and use the cash flow to pay it down over the next 12 months.C) WalkD) Other options???

A hard money lender who works with auctions should be able to get you funded very quickly if you have set things up with them beforehand. 

After receiving the resale packet for the property from the property management company it was identified that the HOA was operating in a monthly deficit and the reserve fund was only at about 32% of what the recommended amount was.

So leverage your time to find deals, and they will fund the project for whatever split you can negotiate.